Last winter, a lawyer representing the Teamsters union made a proposal to leaders at the Justice Department: After 35 years, the lawyer said, it was time for the government to stop monitoring the union.
The outreach, which has not previously been reported, was described by people who either participated in the discussions or were briefed on them, who spoke on condition of anonymity to describe private conversations with the government. The talks paved the way for a motion filed last week by the Teamsters and federal prosecutors in Manhattan that would dismantle what remains of external disciplinary structures established in 1989 to rid the union of organized crime.
If approved by a federal judge, the proposal would be a major victory for Sean M. O’Brien, the Teamsters president, who has leveraged political connections and tough talk to assume outsize power in the union and in the Trump administration.
Last week, at the union’s convention in Las Vegas, Teamsters delegates voted so overwhelmingly in support of Mr. O’Brien’s nomination bid that he was re-elected on the spot to a second term. Mr. O’Brien, 54, is poised to begin his second term as Teamsters president with a clear mandate, a close hold on power and political influence, including the ear of President Trump.
In his profanity-laced acceptance speech to more than 1,700 Teamsters delegates, Mr. O’Brien celebrated the “militancy” that has defined his leadership. He demanded unity, “no more bullshit.” The union’s power flowed from the members up, he said, not the top down. But the chants of “five more years” made it clear who was in charge.
“I’ve got an alpha personality, there’s no doubt,” Mr. O’Brien said in an interview in Las Vegas. “But I do have a tremendous amount of integrity, I’ve always prided myself on doing what’s right for the organization.”
He said he viewed his re-election as proof that he had been “inclusive and transparent” with the union’s members, and the potential deal with the government as a testament not to his force but to his relationships, and to the Teamsters’ demonstrated ability to police itself.
“I mean, enough is enough,” Mr. O’Brien said of the new agreement. “The time was right.”
The prospect of Mr. O’Brien unbound worries some Teamsters and lawyers familiar with the union, who spoke on condition of anonymity to describe sensitive legal matters or because they feared reprisal from union leadership. Even those who said Mr. O’Brien was an effective leader also said he could be a bully with little tolerance for dissent. And while many believe the union should police itself, they fear that without meaningful opposition or independent monitoring, Mr. O’Brien will run the union like an autocrat.
Last week, the day before the union and prosecutors filed their motion before a judge in Manhattan’s Southern District, more than 20 Teamsters filed their own letter in the case, expressing concern that Mr. O’Brien might undermine the independent investigation process.
“There are ongoing cases and investigations involving alleged improper dealings, including concerns regarding election-related conduct within our Union,” they wrote. “For that reason, there is significant need for the independent safeguards preserved under the Court-approved framework to remain in place and fully effective.”
Judge Loretta Preska, who has overseen the case for nearly a quarter-century, has not responded to the union’s request. A spokesman for the U.S. attorney’s office in Manhattan declined to comment.
Mob ties
The outside monitoring of the Teamsters has its roots in a 1988 racketeering case brought by federal prosecutors in Manhattan. They found that organized crime had taken control of the union, engaging in mail fraud, embezzlement, bribery and murder. Union members were intimidated through violence and threats, while corrupt union officers enriched themselves.
In 1989, the Teamsters signed an agreement that barred members from engaging with organized criminal groups and established election procedures for the union. The agreement also established a court-appointed review board to investigate and prosecute claims of wrongdoing and to oversee disciplinary proceedings.
Union leaders and people involved with the case over the years agree that, by the late 90s, most of the mob influence had been rooted out. In 1999, James P. Hoffa, the union’s president, vowed to end the government’s supervision. But problems remained, and the government — specifically, the federal prosecutors, who were in a semi-adversarial position with the union — retained powers over union affairs.
In 2015, Judge Preska approved a new agreement called a final order that paved the way for the Teamsters to assume more responsibility for union elections, internal investigations and discipline. The union can appoint people to the three main roles in the setup: election supervisor, independent investigations officer and independent review officer.
Timothy S. Hillman, a retired federal judge from Massachusetts, was appointed in 2024 to serve as the elections supervisor. Barbara S. Jones, also a retired federal judge, has served as the independent review officer since 2016. Robert D. Luskin, a partner at the law firm Paul Hastings, was appointed as the independent investigations officer in 2021.
The independent investigations role has long agitated union leaders. Mr. Luskin and his team investigated claims of wrongdoing and makes recommendations to the Teamsters board, which can determine punishment.
The 2015 final order called for the Teamsters to create an internal investigative, disciplinary and audit apparatus. Under Mr. O’Brien, that office has taken shape under Frank Hughes, a former Massachusetts State Police officer.
People who have participated in Teamsters investigations and disciplinary proceedings said there was awkward and confusing overlap between the work of Mr. Luskin’s team and that of Mr. Hughes’s team. On a few occasions described to The New York Times by people involved in the investigations, witnesses would speak with somebody from the independent investigator’s office, only to be contacted days later by an internal Teamsters investigator.
Late last year, two Teamsters leaders — including a former international vice president on Mr. O’Brien’s election slate — resigned amid an investigation into their abuse of union funds, and each paid $50,000 in restitution. In February, Mr. Luskin filed a 150-page report detailing how the men had for years enriched themselves through embezzlement, abuse of the union credit card and shorting local union dues, to the tune of tens of thousands of dollars.
Mr. Luskin’s report chided the union’s executive board for letting the men off easy, an “unacceptable resolution” for their “egregious misconduct.”
When Mr. Luskin’s five-year term expired earlier this year, he was not renewed for another. Rather than appoint a new outside investigator, the Teamsters moved Judge Hillman into the role, in addition to his work as elections supervisor.
The moves didn’t show up in any public activity on the docket in Judge Preska’s courtroom. A few weeks earlier, Brian T. Kelly, a lawyer working for the Teamsters, had asked Todd Blanche, then the deputy attorney general, to negotiate an end to the government’s oversight of the union, according to people involved in the case.
The matter was quickly in the hands of federal prosecutors in the Southern District, under the leadership of the U.S. attorney Jay Clayton. While some people involved in Teamsters oversight felt the move was too sudden, there was general agreement that the union should manage its own affairs, people familiar with the discussions said.
The new final order would close the independent investigator’s office on Dec. 31. The role of the independent review officer, still held by Judge Jones, would end in three years. Judge Jones would still have the authority to review some Teamsters disciplinary decisions. She would also continue to review the practices of the union’s internal investigative structure.
Expanded powers
Mr. O’Brien’s re-election marks the first time since the new election structure began in 1992 that an opposition slate of candidates failed to meet the 5 percent vote threshold at the convention to challenge an incumbent.
Earlier this year, a member of the opposition slate filed a complaint against Mr. O’Brien with the union’s election supervisor, saying Mr. O’Brien had violated campaign finance rules by discussing the election, including attacking his opponents, on his podcast, “Better Bad Ideas.”
The episodes involve a lot of profanity. Among the printable things he and his guests say about their opponents are that they are “clowns” and “losers” and “no good.”
The election supervisor ordered Mr. O’Brien to remove the offending episodes from streaming platforms and disclose some sponsorship payments, among other measures.
Mr. O’Brien was elected president of the Teamsters in 2021. He captured national attention in 2022, when he nearly got into a fistfight with Markwayne Mullin, then a Republican senator from Oklahoma, during a labor committee hearing. While Mr. O’Brien made public appearances with Senator Bernie Sanders, independent of Vermont, he soon made overtures to Republicans, including Mr. Trump.
He spoke at the 2024 Republican National Convention, praising Mr. Trump before railing against corporate greed. He has said he was denied a spot at the Democratic National Convention but that he would have given the same speech. That fall, the Teamsters did not endorse a candidate, a blow to the Democrats.
Since then, Mr. O’Brien — and, he says, the Teamsters — have benefited from his access to Mr. Trump, including meetings at the White House. After the 2024 election, he urged Mr. Trump to nominate Lori Chavez-DeRemer, a one-term Republican congresswoman from Oregon and labor ally, to run the Labor Department. She resigned under pressure earlier this year, amid investigations into her abuse of office.
Mr. O’Brien said he had spoken with Mr. Trump on matters such as transportation projects and labor legislation, including a bill passed by the Senate with bipartisan approval earlier this month that would expedite collective bargaining agreements.
“From the Teamsters’ perspective, having a relationship with Trump is extremely important,” Mr. O’Brien said.
With the midterms approaching and 2028 presidential hopefuls starting to test the waters, Democrats and Republicans alike continue to seek the Teamsters’ favor. Representative Ro Khanna of California and Senator Cory Booker of New Jersey, both Democrats, and Senator Josh Hawley of Missouri, a Republican, spoke at the convention in Las Vegas.
Mr. Khanna, who represents Silicon Valley, has been a critic of the concentration of power and wealth in Big Tech, a particular bugaboo for Mr. O’Brien. He received a standing ovation in Las Vegas, and opened with a joke about Mr. O’Brien’s resounding victory. “Ninety percent! Those are Putin numbers!” There was some halting laughter.
In fact, Mr. O’Brien secured 96 percent of the vote.
William K. Rashbaumcontributed reporting.
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